


Holiday Inn

by OsirisApollo



Series: Holiday Inn [1]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, Bottom Dean, Boys Kissing, Castiel In Love, Castiel and Dean Winchester are Cute, Concerned Castiel, Dean In Love, Dean's First Time With a Man, Established Castiel/Dean Winchester, Explicit Language, Explicit Sexual Content, First Time, First Time Bottoming, Fluff, Fluff and Smut, Frottage, Gay Sex, Gentle Castiel, Good Boyfriend Castiel, Good Boyfriend Dean, Hotel Sex, Kissing, M/M, NSFW, One Shot, Oral Sex, Porn, Porn with Feelings, Resolved Sexual Tension, Romance, Sexual Content, Smut, Top Castiel
Language: English
Status: Completed
Published: 2017-01-01
Updated: 2017-01-01
Packaged: 2018-09-13 22:48:10
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,212
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9145546
Author URL: https://archiveofourown.org/users/OsirisApollo/pseuds/OsirisApollo
Summary: On their first official date, Dean finds he is too drunk to drive safely back to the bunker. Instead of taking any chance with his Baby, or his angel, he decides to find a hotel for them to stay at for the night. It's not until the door clicks shut behind them that he realizes the implications of his actions.





	

**Author's Note:**

> I usually write fluff and romance. I have no idea where this came from. I swear. I never do this!  
> Happy New Year!

Everything was working out much better than he had anticipated. Except the drinking. Dean hadn’t meant to drink quite as much as he had. But other than that, everything was perfect.

Their first real date had been everything he’d hoped it would be. He had never had a problem with conversation with Castiel before, and luckily the fact that they were on a real date hadn’t changed that. It had been one of the things he’d been worried about. Needlessly, as it turned out. 

It was just like it had always been between them, except now he could hold the other man’s hand until the food had arrived. He could kiss him softly while they enjoyed a few drinks after dinner. He could even spout off all the sweet soppy romantic crap that had always come to mind before, but had never been given voice.

But he hadn’t meant to drink as much as he had, and it was at a point in the night where they were going to have to abandon Baby and get a taxi all the way home if he couldn’t sober up. That just was not happening. When he suggested that they just check into a local hotel, Castiel had readily agreed.

It wasn’t until he was looking for a nearby dive to crash at that he realized what he had done. They were on a date. A real official date. They had been officially together for months now, but this was the first time since that they were out of the bunker, together, alone. Dean had finally gotten around to taking his angel on a real date, and he planned to end the night in a seedy motel in town.

Nope, that was not happening. Dean might be too drunk to drive all the way back to the bunker, but he was not taking Castiel to a shitty motel. If he was going to be the guy that took someone back to a hotel after a night out, he was at least taking him somewhere nice.

They ended up at one of the big chain hotels, but the room was clean, and well designed, and even had a huge flat screen tv along the wall opposite the beds. Two beds. Not that he and Castiel had never shared a bed before, but this was different. They were doing… whatever it was they were doing now, and Dean didn’t want the angel to think he was trying to pressure him into anything he wasn’t comfortable with. Yes, two beds was a wise decision.

The door clicking shut behind them had an air of finality to it that made the hunter jump a little. Luckily, Castiel was fully distracted by the giant tv, and the fancy reclining chair, and the view of the city from the window. Yeah, this hotel even had more than one floor, and they were at the top. 

There was no mother here, and no Sammy. It was like being on a field trip without a chaperone. Dean had too many private thoughts about this kind of personal time with his angel to feel comfortable now.

Castiel had completed his circuit of the room, and the hunter was still standing next to the door, clutching his jacket to his chest. The angel paused in his exploration as if just realizing that Dean had not yet moved. He gave the hunter a quizzical look as he stepped up to him.

“I just realized how this looks, Cas, and I want you to know that this isn’t what I intended.”

The angel tilted his head in a confused manner. “What do you mean?” He asked, taking the jacket out of Dean’s hands and tossing it on the nearest bed.

“I didn’t mean for this date to end with us in bed, or anything,” The hunter cringed as he said it, realizing too late that the angel probably would have never thought of the implications of a hotel room if Dean had never brought it up.

Castiel hummed and grabbed one of Dean’s hands, tugging him to the bed nearest the window and pressing back on his shoulders until the hunter seated himself on it. The angel stood, staring down at him for a moment before he removed his ever present trench coat, tossing it to join Dean’s on the other bed. 

The hunter stared up at the other man. He must be drunker than he’d thought he was. Maybe he shouldn’t have even been driving to get them to the hotel. He could swear the look on the angel’s face was mischievous. That could not possibly be right.

“Perhaps that was my intention when I agreed to accompany you.” The angel then removed his suit jacket. His eyes never leaving Dean’s.

“What?” The hunter whispered. What the hell was happening?

Sure, they had spent a significant amount of time in the last few months making out. He’d even convinced the angel to let him do a few other things. 

Their mutual hand jobs had been a breath of fresh air after the first month of only making out like teenagers. It had gotten to the point that he probably had his hand around the angel’s dick more often than he did his own anymore. Just last week he’d even convinced Castiel to let him use his mouth to get him off, which had been well enough received that he had immediately repaid the favor.

The thing was, it was always Dean. Dean was always the one that initiated the kisses. Dean was always the first one to stick his hands down Castiel’s pants. It was almost like the angel forgot he was allowed to do those things. He always responded enthusiastically when the hunter did something, but he rarely started anything himself.

“Perhaps I meant for this date to ‘end up in bed’ as you said.” The angel didn’t actually use air quotes, but Dean could still hear them.

“You did?” The hunter didn’t really mean to sound so disbelieving, but he was sure he’d never heard Castiel say anything even remotely sexual, and there was no other way to interpret what he was saying now.

The angel looked down at him with an imitation of his own seductive smile and Dean could not help but feel as though their roles had been reversed somehow.

“If you are not adverse to the idea.” Castiel told him, giving him an out like he always did for the angel before anything got too serious. Seriously? Cas was using all his own moves against him. 

Dean knew he was going to have to regain his footing at some point, and he snatched the angel’s tie from where it had been hanging in the air between them. He gave it a tug and Castiel leaned forward obediently, dropping his lips directly onto the hunter’s.

This was familiar, and Dean was able to regain some of his control with the kiss. He grounded himself with a sweep of the tongue that never failed to make the angel moan softly. He still seemed surprised when Dean introduced his tongue, even though almost every spare moment they had recently was with his tongue in Castiel’s mouth.

Still licking his way into the angel’s mouth Dean pulled him onto the bed, kicking off his shoes and pushing himself farther up for a more comfortable position. He released Castiel’s lips long enough to take a breath and then proceeded to mouth along the angel’s jaw toward the ear that seemed to be his weak spot.

It hadn’t taken Dean long to find that little spot, and it was sure to excite him when Castiel responded to the attention he gave it. The deep groan that reverberated out of the angel brought a smug smile to the hunter’s lips. Now he was back on sure footing. 

There was a pause in activity as Castiel awkwardly removed his own shoes. Dean let his hands wander over the angel’s shoulders. There was a place between the other man’s shoulders that also never failed to elicit a response. The hunter suspected it had something to do with the angel’s wings, but he had never asked. It didn’t matter. All that mattered was the way the other man bucked in his arms as he dragged his hands over the spot. Dean chuckled softly as the angel moaned and his mouth sought the hunter’s again.

They were incredibly good at this. They say practice makes perfect, and Dean could see that it was true. They fit together perfectly. Their mouths fixed seamlessly and tongues engaged in never ending battles. Their chests and thighs lay together like puzzle pieces. Almost as if they were made for each other.

With their thighs as tightly pressed together as they were, Dean could not mistake the angel’s excitement. It was pressed neatly into the dip made by the joining of his pelvis and thigh. The hunter released a moan of his own when Castiel’s movements brought their erections into contact. Even through layers of clothing, it still felt incredible.

The angel was fully on top of him, and Dean spread his legs a bit to make Castiel’s actions easier and more comfortable for them both. It seemed to encourage the angel, and Dean was forced to tear his mouth away from the other man’s as a gasp escaped him. Castiel thrust against him again taking Dean’s reaction as further affirmation that he was headed in the right direction.

At the rate they were going, with the angel taking control of the situation in such an expected way, Dean was probably not going to last very long. He felt he should probably retake control, before he embarrassed himself. He wrapped his legs around Castiel’s thighs and forced them into a roll, where he landed straddling the angel.

He grinned down at the other man. The angel looked surprised by the turn of events, but Dean knew he must have allowed the motion. Castiel had a supernatural strength that the hunter could not hope to compete with, and he had no doubt that if the angel could have stopped the movement with no effort. For some reason the thought only served to further excite him.

Dean wanted to try something they hadn’t yet. Not because it was particularly dirty, but because they always seemed to be in a rush. The last thing they needed was one of the bunker’s other occupants walking in on a situation that could not be immediately rectified. Dean had every intention of taking advantage of the complete privacy they had finally found.

He leaned down to reattach his mouth to Castiel’s as his hands wandered over the fold of cloth where his dress shirt met his pants. It took a little effort to untuck it but he got it done, with a little help from Castiel. The buttons on the damn thing were a nightmare, but he managed those as well. Of course, as he finally parted the fabric he was met with an undershirt. He separated his lips from the angel again to take a breath and complain about the new development.

“Please tell me that is the last layer.”

The angel chuckled as he helped pull the dress shirt off completely. Somehow, Dean had forgotten to take off his tie, so the removal was more difficult than expected. When they finally got down to the undershirt, Dean took a special pleasure in eliminating the new obstacle.

With all they had done so far, they had never actually been fully nude in front of each other. The fear of needing to cover quickly in case of a sudden interruption had kept them mostly clothed through all of their experimenting. This was the first time he would get to see his angel in all his glory, and Dean could not wait.

Frustratingly, when he reached for the belt on the other man’s pants, his hands were slapped away. He glared at the angel, but the look was quickly covered by this own t-shirt as Castiel pulled it over his head. His glare faded. It was only fair, after all. 

This time he was allowed to unfasten the belt, then unbutton and unzip the pants before his hands were once again slapped away. He met the angel’s eyes, and received a pointed look in return. Castiel raised an eyebrow and glanced down at Dean’s own pants and he got the idea. He wouldn’t be allowed to remove the other man’s pants without removing his own first. He sighed and hopped off the bed, dropping his pants as soon as he could without risk of tripping and looking like a fool. He watched as the angel removed his own pants.

It was actually kind of unexpected how hot Castiel was, clad in only his boxers with an erection pressing tightly against them. His chest was nearly hairless, and lightly defined. He had a very dark trail of hair from his belly button to the elastic. It lay between two very defined hip bones that captured Dean’s attention.

“Do you intended to just stare at me all night?” Castiel did that eyebrow raising thing he had picked up somewhere along the way that made Dean’s cock twitch.

“Nope.” He grinned at the angel and quickly lost his boxers as well. He had never been shy about his own body, and wasn’t about to start now. Castiel had already seen all of him anyway. He looked pointedly at the boxers still around the angel’s hips, and watched avidly as they were also removed. There was a redness tinting the other man’s cheeks that Dean found adorable.

He climbed back onto the bed, once again straddling the angel. Their erections brushing as he repositioned himself. Castiel moaned, his head falling back onto the pillow behind him. That was pretty much exactly the state that Dean wanted the angel in, so he deliberately rubbed their erections together again. Castiel thrust up into the motion, seemingly unconsciously, but settled his hips forcefully back onto the bed immediately. 

Dean was confused by the angel’s apparent reluctance to play along, and was even more confused when his hand was slapped away before he could grab Castiel’s erection.

“Dean, I want to try something else.” The angel told him, his voice a little more gruff than it had been only moments before.

“Okay.” Dean didn’t have any reservations about trying whatever Castiel wanted to do.

“I would like to try intercourse.” The angel informed him. 

A very sudden sweat covered Dean’s skin at the thought, but he could not deny that he was intrigued. Especially not with his dick jumping excitedly so close to Castiel’s.

“Are you sure?” Dean felt he had to ask. He assumed that their relationship would progress to that at some point, but he was still startled into inaction at the words.

“Yes, I am quite sure. I have looked into the possibility, and I believe we are ready to take that step.” Castiel informed him seriously. Well, shit.

“You did research?” It would be amusing if Dean wasn’t in the middle of freaking out about the unexpected turn of events.

“Yes. I know that you are a very sensual human, Dean. I knew that if this relationship was to progress, this was likely to happen.” 

An idea suddenly struck the hunter and he huffed a breath of laughter. “Why, Castiel.You dirty bird! Did you watch porn?”

“Yes. I also read quite a bit.” The angel admitted, unabashedly.

The idea was fairly amusing, although Dean had done plenty of his own research. Castiel may not have been the first man that Dean had ever been attracted to, but he was the first one he ever had ideas about going that far with. His amusement faded rather quickly when he thought about some of the things he learned, and the decisions that he had come to during his research.

“Alright, we can try that, if you’re sure that’s what you want.” Dean didn’t want the angel to do it just because he thought that he would have to if he wanted to keep the hunter around.

“I’m sure.” Castiel’s beautiful blue eyes locked onto his, and Dean could read the certainty there.

Dean reached over the side of the bed to dig through his pants and find the lube he had taken to carrying around. Just because they had never done this before didn’t mean that he hadn’t been hoping that it would happen eventually.

He applied the lube liberally to his palm before wrapping it around both of the erections between them. The pause in activity had lessened the excitement a bit, and he squeezed them together, stroking a few times to get the mood back on track.

He lowered his mouth to the angel’s again and they made out lazily as Dean stroked them, not giving them as much friction as either one of them really wanted, but just enough to rebuild their arousal. His mouth explored the angel’s sweet spot again, and he was pleased to feel a twitch from the dick in his hand. He nibbled along the angel’s jaw before reconnecting with his lips.

He then reversed the roll he had used previously, landing under Castiel with his legs spread to accommodate the other man. The angel’s mouth detached from his, then.

“Dean, what are you doing?” He seemed genuinely confused.

“If we are doing this, we are doing it this way.” He pressed upward into his own hand and against the angel’s arousal. 

Castiel closed his eyes at the sensation and moaned low in his throat. When his eyes opened again he still looked confused. As if it had never even occurred to the angel that this might happen.

“Are you sure?” 

Dean rolled his eyes at Castiel using his own lines against him again. “Yes.”

“I don’t mind…” and that was as far as the angel got before Dean squeezed their dicks together tighter and thrust forward again. This time he couldn’t hold back his own moan at the sensation.

“You said you did your research. Show me what you learned.” Dean said it with as much confidence as he could muster. Yeah, he was a bit scared. He’d never done anything like this before, and he knew that Castiel hadn’t either. He knew the angel would never hurt him, though. He trusted the other man with his life on a daily basis. Certainly he could trust him with this.

“If I do anything wrong, you’ll tell me?” Castiel seemed to be more nervous than Dean.

“Yes.” The hunter agreed, although he had no idea how he would know if the angel was doing something wrong.

“If I hurt you at all, you’ll tell me to stop. No matter what.” Blue eyes met green and Dean could see the worry in his partner’s eyes.

“Of course.” He agreed again. He squeezed the hardness in his hands again. “Don’t worry so much.” He grinned as the angel tried not to thrust forward. “This is going to be great.” He hoped.

Castiel shook his head at the cocky tone in Dean’s voice, but he seemed to be thinking now about the position that he had been put in. He grabbed the hand that the hunter had been using to gently stroke them, and forced the grip to tighten around them. The angel squeezed and rocked and stroked at the same time and the moan that tore out of Dean’s throat at the action was completely involuntary. His head fell back against the pillows, and he decided it was time to let Castiel take control of the situation again.

The angel’s mouth fastened onto Dean’s again, and their tongues engaged in another battle. For some reason the action of Castiel’s tongue thrusting into his mouth in a facsimile of the act they were working toward was more of a turn on than the hand around his erection at that moment. He wasn’t really the kind to give up control very often, but it crossed his mind that maybe he should.

Castiel’s mouth began to wander. After one last stroke he released his hold, pushing the hunter’s own hand away. Dean might have complained if the mouth on his chest wasn’t making a fairly clear path. He would much rather have the angel’s mouth than his own hand. 

There was a shuffling of the sheets next to them as the angel’s hand searched for something. It took an inordinate amount of time for the hunter to figure out what Castiel was looking for, being completely distracted by the tongue swiping across one of his hip bones. He could see the tube from where he was lying, and reached for it. As he placed the lube in the angel’s hand, the fingers that closed around it gripped his hand for a moment in thanks. A comforting gesture that went unheeded as a warm mouth closed around the tip of Dean’s erection.

Dean didn’t even attempt to stop the uninhibited moan that escaped at the action. It felt incredible, and the sight of Castiel lowering his mouth onto him was possibly better than anything else he’d ever seen. It was like the idea that the angel was the one with a mouth around his dick was hotter than the actual act. He felt Castiel’s hand brush the inside of his thigh and tried to force his concentration to remain on the angel’s mouth. He knew he had to try to keep from tensing up.

When a finger glanced over his entrance, he tensed. He ran his hands through the angel’s hair in apology, and hope that Castiel would understand. He didn’t want to have to speak. 

It seemed to work, as the finger began to rub in soothing circles around the area. Slowly, the angel began to allow a pressure to the action and by the time the tip slipped in, Dean had already nearly forgotten about the actions of Castiel’s hand. He was immediately reminded. He tensed momentarily, but forced himself to relax fairly quickly. At least the angel was wise enough not to back off. No way would Dean be able to do that again without tensing up.

The dark head hovering over his erection suddenly dropped, and that wonderful heat was covering him completely. Dean groaned intensely at the sensation, and nearly screamed when the throat around him tried to swallow. Where the fuck did Castiel learn to do that?

Even more unsettling was the realization that the angel had used the distraction to press his finger in the rest of the way. He clearly hadn’t been lying when he said he’d done research. Dean hadn’t even realized he’d done it. He took another deep breath as Castiel’s sweet mouth pulled away so the angel could breathe for a moment.

Castiel pulled back a bit farther, and Dean heard a needy moan escape the other man, as he felt the finger inside him withdraw a bit. He watched the angel ogle the movement of his own fingers. The dirty feeling he got from knowing Castiel was watching his finger thrust slowly back into the hunter was, very surprisingly, the good kind of dirty. He allowed the other man to enjoy the view for a couple of agonizingly slow thrusts of his finger before Dean had to get his attention back to where he really wanted it.

“Cas.” The angel’s eyes snapped up to meet his, and Dean rushed to reassure Castiel as the finger inside him retreated at the word. “It’s fine!” It was too late, and the finger was gone. Dean sighed.

“Kiss me.” He didn’t mean to startle the angel so badly, but he’d have to do something to get them back on track. When Castiel pulled back from the kiss to allow Dean to breathe, he took a chance that he hoped he wouldn’t regret.

“Give me two fingers.” The angel’s breath hitched at the words and his pupils seemed to dilate. “But keep, uh you know. With your mouth.” He was not particularly articulate at the best of times, it certainly couldn’t be expected of him now.

Castiel, thankfully, seemed to understand the request, and coated two of his fingers with plenty of lube before returning his attention to Dean’s erection. The fingers circled his entrance in the same pattern the angel had used before, getting the hunter used to the idea of them being down there before trying any kind of penetration. 

Once he had slipped the fingertips into him again, he used the same neat trick of completely distracting Dean to be able to push past the tight ring without the resistance of him tensing up. This time he could not be fully distracted, as there was a slight burning that hadn’t been there the first time. It wasn’t even enough to be considered painful. Just different and new and a little scary.

It took him a moment to adjust to the new sensation, and when he did he came to a very startling realization. He was very close to losing it down his angel’s throat. How he had gotten so close without realizing it, he didn’t know, but he knew he had to do something immediately if he wanted to stop it.

He dropped a hand into Castiel’s dark locks and pulled until the angel’s mouth came off his dick. The glare he received for the action was  _ not _ helping his level of arousal. He tried to take a breath to steady himself, but felt the angel’s fingers retreating again and had to stop the motion. 

He pressed his ass toward the angel’s hand in an effort to nonverbally communicate that the angel should not remove them. The move had an unaccounted for effect. The angel’s hand had not been retreating as quickly as he had pressed back onto them, and the fingers where now much deeper than they had been before. The extra length inside of him, and the girth of the base of the fingers caused the sting he felt to intensify. Of course the twinge of pain that accompanied the action had the opposite effect of what it should have.

His hand flew to the base of his cock in an effort to stop the orgasm he felt building at an alarming rate. He was not about to come before he even got the chance to get fucked by the angel. That was not happening. He squeezed a little harder than was strictly necessary, but he had no intention of letting his body do what it wanted. 

He felt the angel try to withdraw his fingers again. “Don’t!” He could barely hold back as it was, he couldn’t handle any more stimulation right now. Of any sort. “Don’t move.” He told the angel, not bothering to open his eyes. He knew anything he saw was just as likely to send him over the edge.

When he managed to get a couple of deep breaths in, he finally opened his eyes. He groaned at the sight of the angel that was currently kneeling between his thighs, staring again at the fingers Dean hadn’t allowed him to remove. Castiel’s pupils were so blown the blue was barely visible. His lips were swollen and red, and the knowledge that it was because he’d just had them wrapped around his dick was enough to make Dean let loose a hearty moan.

“Are you alright?” Castiel didn’t seem to know what to do at the moment, which was alright because Dean was still trying to calm down enough to be able to continue.

“I’m fine.” He took one more deep breath to steady himself. “Ok, you can keep going. Maybe this time without your mouth.” Because fuck if even the idea of the angel’s mouth at this point didn’t make him want to lose it still.

Castiel’s fingers slowly withdrew, and pressed forward again. The stinging sensation was still there and it helped to relieve his extreme arousal, thankfully. The angel worked his fingers into him a few times before they did a scissoring thing that was new. It wasn’t particularly painful, but it wasn’t really pleasant either. It was mostly just odd, and without the distraction of Castiel’s mouth Dean could concentrate on the new sensations those fingers were bringing out.

When Dean looked at him, the angel’s expression held a bit of concern and he was staring at Dean’s face intently. He realized that Castiel was worried that he was in pain, and he tried to smooth his features. He wasn’t in pain, but he wasn’t exactly filled with pleasure. At least not anymore. He didn’t want the angel staring at him like that, though. He shook his hips a little to encourage Castiel’s gaze back to his nether regions. 

The action had unexpected consequences. He gasped and his back arched off the bed without his permission. Holy shit.

The fingers inside him froze again, but this time Dean consciously thrust himself back onto them. His eyes met Castiel’s and he hoped he could convey without words what that had been all about. Understanding seemed to flash in the angel’s eyes, and his fingers immediately worked to find that spot again. 

On the third try he hit the jackpot. Dean could not believe how good that actually felt, and he let his pleasure be heard, even as he thrust back harder onto the fingers. That was amazing.

This was taking too long, and now that Dean knew all of those websites were not lying about the pleasure of this activity, he was even more eager to get this show on the road. Not really knowing how else to say what he wanted, he just moaned what he wanted into the heavy new atmosphere.

“Another. Come on.” He groaned as Castiel removed his fingers to add even more lube before he pressed them back at his entrance. Dean didn’t even wait for him to slowly press in as he had been doing. He thrust back on the fingers as soon as he felt them against him. He then proceeded to moan like whore as the breach caused the sting to flare again. And apparently he liked a little pain with his pleasure. Who knew?

The angel above him moaned a terribly needy sound at the sight of Dean pressing himself back harder and harder on the other man’s fingers.

“Shit Cas. That feels so good.” He couldn’t help but add to the other man’s suffering. “I can’t wait for you to fuck me.” And that was true, surprisingly enough.

The sound that escaped Castiel at the words sounded more like torture than sex. He was breathing heavily and Dean could see that he was using all of his willpower to keep himself from fucking the hunter before he was properly prepared. Dean was done waiting for the angel to be satisfied though.

He moaned loudly and in a highly inappropriate tone, as he pressed back hard enough on the fingers inside him that the attached hand was pressed into the mattress, no longer in control of the situation. He quickly lost track of his plan to break Castiel’s will as the fingers inside him curled slightly and brushed that spot that made him see fireworks and gasp for air like he’d run a mile. 

When he was able to speak again, he realized he was not above begging at this point. “Please, Cas. Just fuck me already.” 

“Dean.” Holy hell. The angel’s voice was destroyed, a combination of arousal and having Dean’s cock down his throat so many times. “Everything I read…”

“I don’t give a fuck what the internet says. I say I’m ready.” He thrust back onto the fingers again to make his point.

Castiel looked skeptical, but seemed to decide that Dean’s argument was valid. He removed his fingers and Dean got to watch the torturous expression that crossed his face as he coated his incredibly angry looking erection with a generous amount of the lube.

“Tell me to stop if it hurts.” Castiel told him again, and didn’t move to continue until Dean nodded his head in agreement. Fucking angels.

Dean was incredibly glad that he was too turned on to care much at this point. He might have been a little scared when he felt the head of Castiel’s dick line up with his entrance, but he was so horny all he could think was  _ finally. _

A moan tore out of his throat at the same time the head passed the tight ring of muscle. Oh it burned, but he was finally getting what he’d been asking for, and he was not about to stop it now. 

Castiel seemed to be using his limitless patience again, and it took forever for the gentle pressure to allow all of the angel into him. Dean was actually grateful for Castiel’s refusal to just thrust into him like he’d been asking for. At least one of them should keep their head in this situation. And that would not be Dean. 

Once Castiel was in, as far as he could go, he placed a palm on each side of Dean’s head and leaned down to press his mouth to the hunter’s. Dean took the distraction for all it was worth, shoving his tongue into Castiel’s mouth, and wrapping his arms around the other man. He didn’t have to admit that the angel had been right about the prep, but he didn’t have to just suffer his own decision either. He threw himself fully into the kiss, and was rewarded with a swift stroke of his recently neglected erection. The sudden friction made him gasp into the mouth pinning him down. A few strokes later and he had relaxed enough to want to continue.

“Move.” He said against the angel’s lips. Castiel pulled back far enough to look him in the eye, before very slowly backing out a little, and pushing forward again. His eyes never left Dean’s face as he did it again. Then he pulled back a little farther the third time. When he pressed forward again, he changed the angle of his thrust slightly. It wasn’t until the third time he adjusted his position that Dean figured out what he was doing, and his mind was absolutely blown.

The guy had to have absolutely infinite amounts of willpower. He hadn’t had any form of relief from his arousal and had hardly been touched at all. Now, he finally had the opportunity to thrust into a willing body, and he was still too busy trying to make sure of Dean’s pleasure to do it. Holy. Fuck.

Dean decided it was probably time Castiel had a little fun, and he pressed back onto the angel to indicate that he could take more. Castiel didn’t change his pace at all.

“Harder” The hunter told him and then moaned loudly when the angel found that spot he had been looking for. Dean received a smile in response, and then a thrust that actually was harder. It hit the exact same angle and the noise that escaped the hunter was almost embarrassing.

“Shit. Cas. Fuck.” Any articulation Dean might have once possessed was nowhere to be found now. He could only say one word sentences at this point. Castiel hit that spot again, and the hunter could barely form a thought, let alone make one come out of his mouth. 

Dean just moaned, nearly continuously, and clung to his angel. At this point he was just willing to let Castiel do whatever he wanted. He knew the angel would make sure he was taken care of. He just wished he knew how to make sure Castiel wasn’t so focused on him that he forgot to find his own enjoyment.

There was a heartfelt groan above him, and when Dean chanced a glance at the angel’s face he was pleased to see the telltale signs of a man about to break. Castiel’s reluctance was clearly wearing thin. The strain of holding back was clearly visible in every line of his face. His eyes were squeezed shut and there was a thin sheen of sweat forming on his forehead. Dean knew that angels didn’t usually sweat, and he might have worried if he hadn’t already known the monumental amount of effort the other man was currently using.

“Castiel.” The name had the desired effect when the angel’s eyes popped open immediately to stare down at him. “You gotta let go, man. Come on.”

The arms on either side of his head shook for a moment, and Dean knew the other man would break any second. He wrapped his legs around the angel’s thighs and met his next thrust.

“I want you to.” He groaned out, pulling the angel in harder and meeting him thrust for thrust.

That was it. There was a rush of breath across his face and Castiel finally let go of the iron hold on his control. The steady easy rhythm he had established fell apart. His next press was faster and harder than any of before it and Dean nearly screamed as he managed to hit exactly the right spot at what seemed like exactly the right velocity.

“Yes! Fuck!” And he was back to one word sentences, but it wasn’t like the angel was paying attention anyway. Castiel’s teeth were clenched as he slammed into Dean over and over. The air was filled with a whine and it took the hunter a while to figure out it was coming from him. Even after he knew, he couldn’t make it stop. He knew he wouldn’t last long.

Dean could feel heat pooling in his belly, a sure indicator that he was about to reach completion. He tried to warn the angel, but before he could get a word out, Castiel’s hand wrapped around his dick again and he threw back his head with a shout instead.

“Dean,” The angel groaned softly. The sound of his name falling from those wonderful lips was all it took to push him the rest of the way. The hunter pressed his mouth to the arm still next to his face to muffle the sounds he made as his release painted across their stomachs. His body clamped down around the angel, and it was only a stroke or two later when Castiel’s thrusts sputtered to a stop with his own release. The fact that the angel had made it as long as he had was a miracle in itself.

When Castiel’s head dropped to his shoulder, Dean wrapped his arms around him and attempted to pull the rest of him down on top of him too. Castiel resisted only for a moment before allowing himself to fall onto the hunter. The groan that escaped him as he did sounded exhausted, and Dean let out a huff of amused breath at the sound.

They lay like that for a minute, with Castiel’s face pressed into his neck and Dean’s hand rubbing circles over the other man’s back, careful to avoid the sensitive spot so as not to over stimulate him. It was the kind of after sex cuddling that Dean usually liked to avoid, but didn’t have to with Castiel. He planned to keep this one around for a while.

When the weight of the other man on top of him became uncomfortable, he gently pressed the angel’s shoulder in an effort to push him off. He hadn’t really thought it through, and as the angel rolled off his softening dick slipped out, causeing the hunter to draw a startled breath. He hadn’t even realized that Castiel hadn’t pulled out, and the sudden movement on a now very tender area made him wince in pain. 

Castiel was immediately alert and worried, his eyes swept over the hunter’s body as if looking for more wounds.

“It’s fine. I’m fine. I just wasn’t expecting it.” Dean told him, face crinkling at the sight of his own cum decorating his stomach. It was drying quickly, and he would probably have to do something about it sooner than later.

“Are you sure?” Castiel was clearly unconvinced, and now his face held a healthy dose of guilt as well.

Well, Dean was not about to let the angel think he had anything to feel guilty about. He placed one of each of his hands on each side of Castiel’s face and looked him dead in the eyes. “That was amazing. And awesome. And we will be doing that again. Just give me a couple of days to recover.” He patted one of the cheeks with his hand before moving to rise. “Let me get cleaned up and then we can cuddle until your heart’s content.”

Dean grinned as the angel produced a wet washcloth, from god only knew where. He thanked his lucky stars that he wouldn’t actually have to get up as he swiped it across his belly a few times to rid himself of the mess. He even cleaned up the mess he had gotten on Castiel’s stomach, for good measure.

He was just about to curl up with his angel when he felt the slickness between his thighs and realized there was another whole section of mess he hadn’t even touched on yet. He sighed and straightened, throwing his legs over the edge of the bed.

“I’m going to go clean up the  _ rest _ of this mess.” He gestured vaguely to his nether regions as he stood, noticing a significant amount of lube across the covers as well. “We should probably switch beds, too.”

When the hunter came back from the bathroom, the comforter from the bed had been discarded on the floor and the bed near the door was missing one. Castiel had stolen the other blanket and was still laying in the same bad.

“You like this bed better, or something?” Dean asked, crawling under the fresh covers and curling himself around the angel.

“I can see the stars from here.”

It was then that the hunter realized that the curtains were wide open, showing off the city at night, and the field of stars that had the angel so intrigued. If anyone happened to be looking their direction, not that long ago, they certainly got a show.

“Those have been open the whole time, haven’t they?” Castiel tensed in his arms for a moment, and Dean figured he probably hadn’t thought about it before the hunter brought it up.

“Kinky, Cas. Very kinky.” Dean pressed his grin into the skin on the back of the angel’s neck.

There was a relieved huff of amusement from Castiel as he turned in the hunter’s arms.

“That was not my intention.” He said, unnecessarily. He pressed his lips to Dean’s eyelids, that had somehow fallen closed without his permission. His lips pressed briefly to the hunter’s and he whispered.

“Goodnight, Dean.”

“Night, Cas.” Dean managed to get out before sleep overtook him. He knew he’d be able to sleep peacefully as long as he was in the angel’s arms, and with all the good in his life lately he might actually have sweet dreams for once.

**Author's Note:**

> Let me know if you guys enjoyed this... it is not my usual thing at all.


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